Title: Febrifugine
CAS Registry Number: 24159-07-7
CAS Name: (2
S-trans)-3-[3-(3-Hydroxy-2-piperidinyl)-2-oxopropyl]-4(3
H)-quinazolinone
Synonyms: 3-[3-(3-hydroxy-2-piperidyl)acetonyl]-4(3
H)-quinazolinone; 3-[b-keto-g-(3-hydroxy-2-piperidyl)propyl]-4-quinazolone; b-dichroine
Molecular Formula: C16H19N3O3
Molecular Weight: 301.34
Percent Composition: C 63.77%, H 6.36%, N 13.94%, O 15.93%
Literature References: Isolated from the
Dichroa febrifuga Louv.,
Saxifragaceae and from the common hydrangea: Koepfli
et al., J. Am. Chem. Soc. 71, 1048 (1949); Ablondi
et al., J. Org. Chem. 17, 14 (1952). Identity with b-dichroine: Fu, Yang,
C.A. 43, 1530a (1949). Structure: Koepfli
et al., J. Am. Chem. Soc. 72, 3323 (1950). Synthesis: Baker
et al., J. Org. Chem. 17, 132 (1952);
18, 178 (1953); Koepfli
et al., US 2504847 (1950 to U.S. Gov't); Baker, Querry,
US 2651632 (1953 to Am. Cyanamid). Config: Hill, Edwards,
Chem. Ind. (London) 1962, 858. Revised stereochemistry: Barringer
et al., J. Org. Chem. 38, 1937 (1973).
Properties: Dimorphic crystals: needles from ethanol, mp 139-140°; from chloroform, mp 154-156°. [a]D25 +6° (c = 0.5 in chloroform); [a]D25 +28° (c = 0.5 in ethanol). Freely sol in methanol + chloroform, water + ethanol; slightly sol in water, ethanol, acetone, chloroform. Practically insol in ether, benzene, petr ether. LD50 orally in white mice: 2.5-3.0 mg/kg (Koepfli, 1949).
Melting point: mp 139-140°; mp 154-156°
Optical Rotation: [a]D25 +6° (c = 0.5 in chloroform); [a]D25 +28° (c = 0.5 in ethanol)
Toxicity data: LD50 orally in white mice: 2.5-3.0 mg/kg (Koepfli, 1949)
Derivative Type: Dihydrochloride monohydrate
Properties: Crystals from 90% ethanol, mp 220-222°. [a]D25 +12.8° (c = 0.8).
Melting point: mp 220-222°
Optical Rotation: [a]D25 +12.8° (c = 0.8)
Therap-Cat-Vet: Coccidiostat.
